'Jimmy Kimmel Live!:' How Bigger, Bolder Music Bookings Are Making Noise in Late-Night

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Which band drew 16,000 to the "Kimmel" outdoor stage? Who's the rapper that dropped trou for the cameras? Why have Def Leppard never been back on the show? Music booker Scott Igoe explains the method to his madness.

Music acts on late-night were long seen as the lowest rung on the booking ladder, what with audience drop-off sliding as much as 25 percent during a show's last quarter hour. But in recent years, the competition for name artists has heated up immensely as have creative expectations beyond the time these musicians spend onstage. Look no further than the Jan. 3 episode of Jimmy Kimmel Live! on which Josh Groban sang Kanye West's tweets in his signature operatic style or when Eminem taught the host how to rap in May 2009.

"We were always doing crazy stuff," says music booker Scott Igoe, a former assistant to another Jimmy -- Iovine, chairman of Interscope Records -- who's been with Jimmy Kimmel since Day 1, when he flew in Coldplay on Super Bowl Sunday. The next night, 50 Cent made his network TV debut on the couch before performing "In Da Club," his soon-to-be-hit. "We didn't have guests, so we would put rockers on the couch, or do skits with musicians, or make Snoop Dogg a co-host," he says. "You'd see a rapper on Kimmel once a week, so hip-hop music exploded on our show. It's one of the things that set us apart."

Indeed, where Jimmy Fallon fights to be first, like recent bookings of indie darlings Odd Future and Beach House, Conan O'Brien demands unflinching loyalty, as in multinight residencies by the likes of White Stripes and the Strokes, and Leno and Letterman lock in marquee acts early, Kimmel looks at the big picture -- literally: an outdoor stage that accommodates 1,000 fans and allows artists to play five songs or more, not to mention off-site happenings that are pure spectacle.

Perhaps the best example was a 2009 performance by Depeche Mode outside Hollywood's W Hotel that drew 16,000. It remains the largest outdoor music gathering in Los Angeles history "with very few fights and no arrests," Igoe boasts. The seven-song production carried a hefty price tag of $400,000, much of which was picked up by the W as a way to promote its just-completed residences (sponsors Bud Light and Summit Entertainment chipped in as well), but it made for destination viewing. "Everybody won that night," says Igoe. "It was just magic."

Igoe has three rules when it comes to a performance slot: First, know your target audience. "A lot of bands have passed up Leno not because of the numbers but because it didn't look cool," he says. Second: Do right by your fans. "The only bands I've ever heard booed were Hoobastank, who only played two songs on the outdoor stage because they had a flight to catch, and Def Leppard, who came on and did seven songs, not one of which was a hit," Igoe recalls. "Both have never been back." Lastly: Be into it. Says Igoe, whose wish list still includes Elton John, Stevie Wonder and Rush: "I don't care if it's Steve Martin, Elton or Linkin Park, if you're, like, 'I dread going on Jimmy Kimmel,' then suck it. We don't want you on the show. Go and be the 107th band to play with the Roots, then."

More on the music of Jimmy Kimmel Live!after the jump, where Igoe runs down five additional unforgettable bookings.